


Kindergarten Rules

by writerposer



Category: Supernatural
Genre: Abusive John Winchester, Anxiety, Dean's the best dad, Fluff, Kid Fic, M/M, Past Abuse, but also so much fluff I promise, john was the worst dad, teacher!Cas
Language: English
Status: Completed
Published: 2020-07-11
Updated: 2020-07-11
Packaged: 2021-03-05 03:35:25
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 8,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25197817
Author URL: https://archiveofourown.org/users/writerposer/pseuds/writerposer
Summary: When Dean drops his daughter Emma off for her first day of kindergarten, Dean never expected that his childhood best friend Cas would be her teacher. If Dean can get over his bullshit, maybe the two have a shot at being something real.
Relationships: Castiel/Dean Winchester
Comments: 8
Kudos: 151





	1. Chapter 1

“The sun is shining too goddamn brightly,” Dean grumbled to the near perfect scrambled eggs. Dean grumbled all throughout breakfast. And he grumbled on the miraculously traffic-free roads. He grumbled while watching the smiling pedestrians. He grumbled all the way up to the maroon and gold sign that proclaimed “Washington Elementary School,” 

Dean’s mouth went dry. His speech and his legs failed him. The only thing that propelled him forward was the tiny, yet forceful hand secured in his. 

“C’mon Daddy, we’re gonna be laaate,” Emma called from somewhere under an impossible mop of blonde hair through the gap in her teeth. 

Dean re-engaged his legs with great difficulty, trying to prolong the inevitable for as long as possible. Kindergarten. His baby girl was starting school, and it was time to face it. 

“Ok, right, yeah, let’s go,” Dean managed to choke out, as they strode past the sign, across the cobbled courtyard, and into the fluorescently lit office. 

Together they approached the faux-wood desk, and Emma stood on her tip-toes to try and read the little placard that read “Charles Shurley”, while Dean forced a smile. Charles, or Chuck, as he immediately corrected, handed Dean the paperwork, and pointed straight to the end of the hall. Dean felt a slight air of judgement in the air, seeing as he waited until the actual first day of school to finish registering his daughter. He just couldn’t bear to see her grow up so quickly, and dragging his feet did nothing to stop her from sprinting forward. 

Chuck leaned over the desk, and to Emma he said sweetly, “You’re going to be in Mr. Novak’s class. He is very nice.”

Emma nodded seriously, and then proceeded to tug Dean toward the door that Chuck had indicated. 

“Novak,” Dean chewed over in his mind, “No, it couldn’t be. We’re states away from Lawrence.” 

Dean managed to corral his daughter before she barged into the front door. “Listen kid, no matter what happens today, I want you to know that Daddy loves you,” he smiled brightly, and was greeted by his favorite, gap-toothed, smile. 

“I know,” Emma said, before she raced ahead of him inside, and promptly fell on her face. Dean lunged forward to rescue his daughter, as a dark-haired blur attempted to do the same, resulting in both men knocking foreheads, and falling down themselves. By the time Dean looked up, Emma had already revived herself, and was shyly sidling up to the first table she saw. He smiled slightly, before turning his attention to the man in front of him, and the very blue eyes. 

Those eyes were currently blown wide in surprise, not because of the blunt impact that his head just suffered, but because of recognition. 

“Cas?” Dean smiled in pleasant disbelief.

“Hello Dean.” 

Castiel Novak aged well.  _ Really _ fucking well. What had been an incurable blight of bed-head on the dorky kid became, became,  _ sex hair  _ on this, Dean did the math quickly, 34 year old man. His navy tie hung loosely, resting on his subtly defined chest. His voice reverberated through Dean’s very  _ soul _ and it took the man a few seconds too long to register that the low, lovely, and powerful, voice was forming words, and words directed at him nonetheless!

“... and I never let myself entertain the notion that I could possibly be teaching my childhood best friend's daughter, so I quashed my enthusiasm, yet, here you are,” Dean realized that Cas was rambling, which was a very un-Cas thing to do, and, was that a blush? 

Dean realized it had been entirely too long since he had spoken, and he was just staring like a dumbass at the other man. 

"Mr. Novak, why are you on the floor?" A tiny brunette called from the colorful table at which Emma sat herself down at. 

"Oh, I was just being silly, that's all Krissy," and Cas hoisted himself up, offering another hand up to Dean. 

  
Dean hesitated for another moment, before firmly grasping the surprisingly strong outstretched hand. 

“It’s really good to see you Dean,” Cas paused, before looking over Dean’s shoulder, “but an alarming number of five year olds and their mothers are streaming through that doorway, so can we pick this up later?” 

“Oh, yeah of course. I have to get to work myself,” Dean thought quickly to his job at Sandover Bridge & Iron, and cringed at how much he had to accomplish before picking Emma up from school. 

“Excellent,” Cas smiled, and quickly scribbled his number on a napkin, in a purple crayon. Dean smirked and pocketed it, before searching for Emma to say goodbye. His eyes landed on her, animatedly chatting to an enraptured brunette, who Dean assumed was Krissy, and smiled proudly. 

Somehow, Dean left the school in a good mood.

Even stepping into his office, which Dean was convinced was slowly corrupting his soul from the inside out, felt wasn’t so bad, with the imagined weight of Castiel Novak’s number in his pocket. He suddenly had a much higher tolerance for his boss, Zachariah's bullshit. Schmoozing clients and eating rabbit food was almost bearable, and he only fantasized about a double bacon cheeseburger three times instead of the usual six. 

When 2:45 rolled around, Dean leaped out of his chair, and ignored his assistant’s laugh as he raced out the door. Dean arrived exactly at three, when an army of children fled the school, and ran to the playground adjacent to the school, to await their doting parents. 

Dean searched for Emma, while keeping an eye out for Cas as well, when he spotted them both, Emma animatedly speaking, with her hands often flying above her head in her excitement, and Cas smiling amusedly. Dean strode up to the pair, and before he could utter his half-baked one-liner, Emma wheeled on him. 

“DADDY! MR. NOVAK WAS YOUR BEST FRIEND!” and jumped up into Dean’s awaiting arms. 

Dean chuckled, “He sure was sweetheart. Mr. Novak, Uncle Sam and I met in elementary school,” Dean looked up, and winked at Cas, and was delighted at the blush he received.

“Did you make any friends today?” Dean asked.

“I met Krissy, and Jack, and Kevin, and-”

Dean let Emma ramble on as Cas released his kids to their parents, one by one. Dean could have stood and watched Cas all afternoon, but soon the rest of the kids were gone and Cas was heading back to them. Dean tried to calm down, but before the two men could catch up, Emma started to give the tell-tale wiggle, which could only mean that the floodgates would soon open. 

“I’d love to catch up Cas, but I don’t think this one is going to last for much longer,” Dean said with a sigh. 

Cas nodded in grim understanding, “Godspeed. I hope you call.”

Dean gave a quick nod to Cas, before quickly carrying Emma to the car before any tragedy could befall his car seats. By the grace of God, the little girl made it to the potty on time. 

Dean only had an hour with the girl to finish debrief on her first day, apparently she made fifty friends and learned a million numbers, before he had to drop her at her mother’s for the weekend. Outside Lydia’s door, Dean dropped a kiss on her forehead, and a quick wave to Lydia before driving back home. His, suddenly empty home. Empty with his 

“I could call Cas,” he thought, “Why shouldn’t I call Cas? He told me he wants me to, I should call him.”

Dean paced more, suddenly gripped with indecision, the years between them feeling suddenly vast. 

It took him a few hours of dawdling, and maybe a shot or two, until he had Cas’s number in his hands, and suddenly he was dialing, and before Dean could take it all back, an impossibly deep voice was greeting him. Soon plans to go out, “catching up drinks” as Dean eloquently stated before smacking his forehead, and hanging up. He shouldn’t have suggested drinks, what if he said something stupid? 

Why was he freaking out so much? It was just Cas... albeit an older, more confident, and downright handsome version of Cas. Could he possibly have feelings for this man? Dean hadn’t had a real relationship since Benny, and he still had trouble visiting that loss, even if the two men were friends now. Even Dean’s relationship with Emma’s mother Lydia hadn’t been much of anything. Emma was simply an unplanned result, a perfect, wonderful, blessing, but an accident regardless. 

Cas, well, that breakup would be on a whole other level of destruction. And why was he already imagining the two of them dating? Cas was probably straight. Maybe even married. Why would he want Dean? He was just a stupid pencil pusher with no life outside his kid. What if he didn’t even want to be friends with Dean? He had seemed happy to see him earlier, but maybe that was just politeness, nostalgia for an old friend, keeping it pleasant for Emma’s sake. Dean could have spent the next two days pondering the risks and rewards of meeting up with Cas, but the clock was ticking down rapidly to when he said he would meet Cas, so he sucked it up, and hopped in the car. 

He arrived at The Roadhouse just in time to see Cas settle into a booth. Dean took several deep breaths, and then slid next to Cas. 

“Hey stranger,” Dean said, and then cringed at himself. 

Cas just beamed back, “It’s good to see you.”

The waitress arrived with two beers without Dean asking. He raised the bottle in thanks, taking a big swig.

“You come here often?” Cas said seriously, and Dean almost coughed up his beer. 

“The waitress appears to know you. Do you have a nice rapport with the staff because of your frequent visits?” Cas clarified, slightly sarcastically, his mouth forming a small smile. 

“Oh, yeah. I uh, come here on Fridays, usually,” Dean said, suddenly embarrassed. He didn’t want Cas to think he had turned out like John.

“Funny, I’ve lived here going on five years, and never even saw this place. It seems you have a knack for gravitating to the very best establishments,” Cas said as he sipped his beer, smiling slightly.

Dean tried to relax and settle in. This was Cas. What did the years matter for a true friend anyway?

Four beers later, the two were laughing like they did when they were kids, slowly learning what they had each been up to for the past twenty years, after Dean’s family left Kansas. Mary took all of their hardship in stride, and put both Dean and Sam through school, with Sam getting a partial scholarship to Stanford, and Dean helping out by taking odd jobs in garages. Sam was still out there, living in Pasadena. 

“He’s the youngest partner at his law firm, and had a baby on the way,” Dean smiled.

“That’s great Dean,” and Cas did the thing with his eyes and his hand was on Dean’s shoulder and Dean thought he just might die.

Cas told him about how he left his oppressive family by fleeing to the University of Chicago for school on a full scholarship, only keeping in contact with Anna and Gabriel. After years on the business track, his father's influence still weighing heavily on him, he eventually switched over to education, and found his calling in early childhood education. 

Dean felt his heart swell, thinking of Cas growing and coming into his own, finding his calling. 

“Emma already loves you,” Dean said.

“Good, I would hate to have any Winchester hold me in contempt,” Cas said.

Their knees were touching and Dean swore Cas was looking at his mouth, and soon enough, the two were stumbling outside to hail cabs, drunk and happy betting to see who could get one first. Dean managed to stop one first, winning the little competition, and in a show of good sportsmanship, allowed Cas to get in. Dean leaned down to close his door for him, and he found himself looking, well staring, into the impossible blue of what could be, and soon he was kissing Cas, and Cas was kissing  _ back,  _ and his hands were on Dean’s face and then the fucking taxi driver was yelling at them so Dean backed off. Cas smiled back up at him, and gently shut the door of the cab in what he hoped to god was a cool move. He let out a small sigh as he watched it speed off, and he knew he was already in far too deep. 

Dean panicked on the way home from the bar. He paced for what seemed like the rest of the weekend. He didn’t call Cas. Did Cas want him to call him? Why didn’t Cas call him? On Monday morning he found himself wringing his hands at work, after Lydia called and let him know that she had dropped off Emma, and that her teacher “seemed nice, yet distracted.”

This was his childhood best friend. They’d spent countless hours spent at slumber parties, raising hell around the neighborhood, emptying out each other’s fridges, and being there for each other when life at home got too hard. This was Cas, who would also probably be the only friend he made in town for a while who he didn’t have to keep buying beers from to hold a conversation. The boy that he grew up with, was the man that he... that he  _ kissed _ two days ago. And sure, he had been thinking about doing a lot more than kissing after he had stepped into that classroom and laid eyes on the man but still, it was  _ Cas,  _ and he kissed him  _ back. _

Dean ran his hands through his hair as he stared out of the window, at his brand new 35th floor office view of his brand new city. He found it loathsome. Dean wished he were elbow deep in a needy Cadillac, closing the hood with a satisfying click, and watching the owner drive off with their newly revived baby purring. He longed for the feeling of grease on his hands, doing something concrete to help his fellow man through the much less complex machine, not making phone calls day in and day out to make a billion dollar company even richer. 

Dean’s daydream was broken by the screeching phone on his desk, and he settled into his chair to answer what was sure to be another devastatingly boring call about iron sales. As he picked up the phone, his eyes landed on the smiling photo of Emma on his desk from last summer at Bobby’s, and he remembered why he put up with all the bullshit in the first place. 

When it was time to pick up Emma, Dean hurried to gather his things. He heard a knock on his door, and his stomach dropped. He turned slowly, and sure enough, his douchebag boss, Zachariah, was standing in the threshold of his office wearing that smug, shit-eating grin. 

“Before you cut out Winchester, I'd like you to proof this little report here,” he said, the fat from his cheeks shifting into what he believed to be an innocent facial expression, while he tapped the thick manilla folder.

Dean assumed his work persona, and said in his best salesman voice, “Is it possible that this could wait until tomorrow Mr. Adler? I have to pick up my daughter from her kindergarten class,” 

“No can do buddy, I need this report read yesterday. It shouldn’t take too long, and you can be with little Hannah in no time,” Zachariah smiled like he was doing Dean a favor, and handed the folder to him roughly. Dean slunk back to his desk, and quickly opened up the folder, while pulling out his phone to text Castiel that he would be late, only to have the low battery sign flash at him moments before the screen went dark.

“Fucking perfect,” Dean grumbled, as he rushed through, editing only one sentence in the whole twenty-fucking-page near- perfect report, and hurriedly dropped it on his secretary’s desk. 

By the time he reached the school, after dozens of honking horns and traffic violations, he was about 45 minutes late. The small playground outside the school was vacant, so Dean awkwardly parked and rushed inside. Dean paused in the doorway to Emma’s classroom, simply lost in the beautiful simplicity of Cas reading to his child, and Emma staring up at him like he had an entire world in his hands. 

“Lucy ran out of the empty room...” Cas waxed, holding court, before he saw Dean in the doorway. Emma saw Cas break in concentration, and then turned around.

“Daddy!” Emma scrambled to her feet, running as fast as her slightly chubby legs could carry her, straight into Dean’s arms. 

“Hey Ems, sorry it took me so long,” Dean smiled as he scooped up his daughter. 

“Hello Dean,” Cas smiled at him, but looked slightly weary. 

“Cas, I am so sorry, Zach, my boss, handed me a report as soon as I got ready to leave and my phone died and -” Cas held up his hands in a placating gesture, effectively cutting Dean off. 

“It’s no problem, I was just showing Emma the magical world of Narnia. Ideally I would have started with “The Magician’s Nephew,” but unfortunately I left it at home.” 

Dean grinned, remembering the many hours that Anna, Cas’s older sister, would spend reading that series to the youngest Novak, and by proxy, Dean and Sam. 

“I really do appreciate all the extra time you put in. You could’ve easily pawned Emma off to the traffic monitor or the frankly terrifying women in the main office.” 

Dean felt the butterflies in his stomach begin to take flight, and before he lost his nerve, “Let me treat you to dinner tonight, to make up for it. Emma and I usually eat out on Monday nights, it would be great for you to join us.” 

Before Cas could respond, as some color invaded his cheeks, Emma squealed, “Mr. Novak is gonna come eat! Mr. Novak is coming to dinner!” 

Dean looked up from his daughter beaming, and hoped he didn’t look too desperate. 

Cas hesitated for a moment, and Dean felt his stomach make a hasty exit from his torso and attempt to escape through his feet, before Cas said, “Well if you insist.” 

Dean put Emma down, and she ran to the corner of the room to get her things. 

“Damn right I insist Cas,” Dean took a step closer to the man, suddenly bold, “I haven’t stopped thinking about Friday.”

Cas’s face became even pinker, “Me neither,” and he paused, seeming to ponder something, then said “Emma’s mother, is she, are you...” Cas trailed off, before he finished his thought. 

“Oh God no, she is totally out of the picture. Well, not  _ totally _ ,” Dean gave a meaningful glance over to Emma, where she was quickly slipping on her velcro jacket, “Lydia and I were never serious, and the only reason I even still see her is because of that one over there,” Dean smiled when saw Cas’s features, previously schooled into a careful mask, dissolve into relief.

“Good. Because as I'm sure you remember, I don’t like to share.” Cas’s smile became very different, and Dean shuddered slightly. Cas’s smile transformed from sinful, to victorious, and finally to innocent as he laid eyes on Emma, all suited up and waiting by the door, hopping from one foot to the next. 

“Let’s get out of here,” Dean composed himself, and the three proceeded out of the building. 

Dean could get used to this. Everything is so  _ easy _ with Cas. The three were sitting at a table in Dean and Emma’s favorite diner. Emma was animatedly narrating the plot of the movie she and her mother had seen last Friday, and Cas listened to her intently while eating his hamburger. Dean smiled absent mindedly at the two, wondering how he had ever hesitated for a moment in embracing this new chapter in his relationship with Cas. He fit into Dean and Emma’s world so well, it was a wonder that they hadn’t noticed his absence all this time. Every now and then Dean’s knee would brush up against Cas’s, and at first he recoiled, but now they rested lightly on one another. 

When the check came, Cas took out his wallet, and Dean shot him his patented death glare until he put away the offending object. 

“My treat. I kept you waiting,” Dean took out his credit card and a few bills for a handsome tip. 

“Dinner with you two is treat enough,” Cas said, getting up, and helping Emma out of her high chair. As the three left the restaurant, Emma grabbed both Dean and Cas hands, and the two pulled her up with every other step, Emma letting out squeals of delight each time her feet left the earth. They reached Dean’s car, a sensible Prius which he hated, but was safer for Emma than his old Impala, and he snapped Emma into place in the back, before turning around to Cas, suddenly feeling self conscious. How did he tell Cas that as much as he wanted to kiss him, there was no way he could do that in front of his kid so soon in a relationship. 

As it turns out, Dean didn’t have to say any of that out loud, because Cas simply took Dean’s hand and squeezed. 

“I’ll see you two tomorrow,” His voice rumbled, and the butterflies occupying Dean’s stomach decided to dive bomb his gut all at once.

“See ya Cas,” He smiled. 


	2. Chapter 2

Lawrence, Kansas

_ 29 Years Ago _

Dean stuck his thumb firmly back inside his mouth as soon as John slammed the front door. From his car seat he could see Mary’s shoulders slump slightly, before she hauled herself up. The tired blond woman twisted back, her painted smile melting into a genuine one at the sight of her darling eldest boy, all dressed up for his first day of school. Dean temporarily plucked his thumb from his mouth to beam back at his mother, missing front teeth only adding to his charm. Mary slowly pulled out of the driveway, and Dean closed his eyes, feeling the familiar and unfamiliar curves in the road, leading him to his new elementary school. 

“Ok baby, we’re here!” Mary was suddenly a foot away from Dean’s sleeping face, he had been lulled into a quiet slumber. Dean woke with a start, and eagerly climbed out of their black minivan. He waddled in his brand new jeans, with his brand new school supplies weighing him down, to pose in front of his brand new school. Mary snapped photo after photo, with the last few being intruded upon by an oblivious little boy in a tan trench coat, a dark blue tie, tan slacks and a white button down, walking right through them. 

“Castiel!” An angry voice rang out, and the dark haired boy stopped dead in his tracks, his posture suddenly rigid, still smack in the middle of Mary’s photograph. The blue eyed child turned on his heels, head first facing the man that Dean assumed was his dad, the five year old recognized the tone and subsequent fear mirrored in the other boy, and Dean’s immediate reaction was to freeze as well, remembering John from that very morning. 

The tall man, with jet black hair that matched his son’s, turned to Mary and barely mustered the courtesy to smile as he said, “Apologize to this woman. You have just ruined her photograph.”

Castiel noticed Dean and his mother for the first time, whipping his head back and forth nervously, before lowering his eyes, and beginning to mutter, “I am so so-” before Mary cut him off with a kind smile and a swift hug. Castiel seemed flabbergasted, but soon caught on that he was supposed to hug back. Mary rose up, stuck out her hand, and suddenly her smile seemed much less sincere as she said, “How do you do, Mary Winchester.”

The man shook her hand strongly, some of his disdain seeming to slip away as he felt how firm Mary’s hand was, but still introduced himself only as “Mr. Novak.” 

When the two broke eye contact, Castiel stared up at Mary in shock and awe, and barely noticed when the green eyed boy sidled up next to him, and stuck out his hand halfway, with a muttered, “I’m Dean.” 

“Hello Dean, my name is Castiel,” the boy repeated robotically, as if rehearsed.

Dean rolled the name over in his mind a few times, and considered the boy in front of him carefully. He knew from TV that if he befriended a dork on the first day, he could become a dork too! Then the older kids would push him into lockers, or give him swirlys, or even an  _ atomic wedgie. _ Dean stared deeper into that lost boy's eyes, and decided that if he had looked so happy and so surprised to get a hug on his first day of school, he must not get many hugs from his own mom. 

So Dean shoved all of his misgivings to the side, and shouted, “Nice to meet ya Cas!” and threw his arm around the startled boy's shoulders. Mary squealed slightly, and began snapping more photos. 

“I, um, see you have everything under control here,” Mr. Novak intruded on the moment, and Mary fought hard to keep her glare inside, “I am late for work. Castiel-” Cas stood rigidly once more, at attention, “Be a good boy.” 

Both Mary and Dean waited for the seemingly inevitable “I love you,” but it never came. Cas seemed to not even expect the near standard sentiment, and Dean was so moved that he did the first thing his five year old brain could think of, he wrapped Cas into a bone crushing hug. Cas was as surprised at his second hug of the morning as his first, and so he neglected to pay any mind to his father who stalked off without another word. 

“What an asshole,” Mary grumbled under her breath, before saying out loud, “Okay Cas, I guess you’re with us for the morning. Let’s all head inside, alright hon?”

Cas nodded seriously, and if he silently clutched onto Dean as they entered the threshold of the building, no one mentioned it. 

A nice man with a beard, Chuck was his name, directed them down the hall, to Mrs. Jody Mills room. 

As luck would have it, the two boys were pushed into the same class. Dean soon forgot his original hesitance in picking up Cas. Entering the bright classroom and waving goodbye to his mom suddenly made him very thankful to have a friend right off the bat. Dean watched as the other kids looked back and forth nervously, and Dean gave Cas a smug grin, as if they had outwitted everyone else there. Cas smiled back meekly. 

The morning went by smoothly. Dean was completely enraptured by Mrs. Mills, he got to sit next to Castiel on the rug, and secured a great spot for nap time right by the blocks for easy access. Post nap-time, Dean rushed to the legos, and sat in a heap next to Lisa Braeden, who had managed to beat Dean to the pit. 

“Cool shirt,” he said quietly, as he started his castle, and Lisa stared down at her superman shirt, that was under her denim overalls. 

“Thanks. Cool sneakers,” Lisa said, pointing to Dean’s light up sketchers. 

Dean smiled extra wide then, pleased that he had convinced his Dad to get them for this very occasion. Dean slowly tried to muster the courage to ask Lisa what her favorite color was, when he heard a familiar voice yelp. His head whipped up, to see Cas cornered by the books, being poked by Gordon Walker. Cas had his head down, trying vainly to keep reading “Go Dog Go.” 

Dean rose to his feet unsteadily, staring down the situation. Gordon just plucked the book from Cas’s small, chubby fingers, and Dean could see his shoulders shake, showing that full on waterworks were only moments away. 

“What are you gonna do nerd? Cry?” Gordon taunted.

This was exactly what Dean feared. 

If he went over to help out Cas, then Gordon and guys like him will call him names too! Dean looked around for Mrs. Mills, but she was nowhere to be found. He looked down at Lisa, who was now staring at the scene unfolding in front of them, unlike the rest of the class. 

Dean waited for a moment longer, and before his brain could come up with a different solution, his three and a half foot frame was marching toward Gordon. 

“Hey!” he shouted, and both boys whipped their heads to him, Cas with tears in his eyes. 

Dean decided there and then that anyone who liked making Castiel cry was not someone he should worry about not liking him. 

“Jerkface! Leave my friend alone!” Gordon’s eyes went slightly wide, but did not step back. His smug face settled into a sneer. 

“Oh, well then I guess you’re a nerd too!”

Dean’s face felt hot, and he could sense the rest of the classroom watching them. Before he could decide on his comeback, he felt a presence next to him. Lisa was standing to his left, her serious demeanor counteracting her black pigtails and overalls. 

“If Dean’s a nerd, then, I’m a nerd too!” She spoke defiantly, hands on hips. 

Gordon felt his hold of the situation spiraling, and inched slightly away from the now more surprised than scared Castiel. 

“You’re just a dumb girl!” Gordon cried, his voice rising even higher. 

Victor Henriksen appeared on Dean’s right, lollipop in hand, Captain America’s shield proudly on his chest.

“I’m a nerd,” he said calmly.

Slowly, the rest of the class filed next to Dean and Lisa, forming a tiny, yet mighty, army of nerds. Gordon looked around, suddenly worried, and he turned and ran into the single stall bathroom on the opposite side of the classroom. 

Dean wrapped his arm around Cas, and the classroom erupted into cheers, that was immediately suppressed when Mrs. Mills re-entered, water in hand, shushing them. 

“Thank you Dean,” Cas said quietly. 

“Anytime buddy.” 


	3. Chapter 3

Lawrence, Kansas

_ 22 Years Ago _

“Do you wanna come to my house?” Dean mumbled out of breath as he shoved his somewhat greasy hands into the pockets of his jeans. He had rushed over to Cas’s house straight after helping his Dad out at the garage, not even bothering to stop at home to change. He couldn’t wait to give Cas his thirteenth birthday present, currently resting in the pocket of Dean’s jacket, and also to taste some of his older brother Gabriel’s legendary chocolate cake (three different types of chocolate were integrated into the frosting  _ alone _ ). 

Dean had rounded the corner onto the giant hill which held the homes of the rich and powerful of the community, the Novak’s mansion resting on the very pinnacle, like a castle on high. He was about halfway up the hill, when he saw a hunched figure cradling itself on Novak's lawn, apparently in a fetal position. Dean broke out into a run, just as a black car that Dean recognized as Mr. Novak’s pulled out of the Novak’s three car garage. The vehicle did not pause as it sped from the long driveway, not even a wave at Cas curled up at the end of the drive. Dean’s vision zeroed in on Cas, his lungs burning, his feet barely catching him as he sprinted up the uneven sidewalk. 

Finally, Dean made it to the end of the walkway, huffing and puffing, hovering over Castiel, shoving his hands in his pocket and doubling over, in a vain attempt to catch his breath. Cas looked up, his blue eyes twinkling with unshed tears, and Dean simply blurted, “Do you wanna come to my house?” 

Cas parted his lips to answer, but promptly shut them as the escalated yelling from within the Novak mansion reached the two boys. Dean tore himself from staring at Cas’s red lips, and glanced for a moment at the white mansion. He could hear the shouts of Michael and Luke, Cas’s older twin brothers. Distinctly absent was the voice of Castiel’s mother, who could usually be heard shouting over the rest of them, during times when the pressure cooker that was the Novak’s finally popped. Cas seemed frozen to the spot, staring at his home, at his life, and the tears that occupied his eyes threatened to rain down. 

“That’s it, c’mon buddy,” Dean grabbed the boy by the armpits, and hauled him up. Despite Castiel being a few months older than Dean, the younger boy still a had a few inches on him, and could manhandle him when he needed to. 

Dean somehow led the dazed Castiel away from his broken castle on high, back to the bottom of the hill, with Cas gripping Dean until so tightly his arm felt numb. Together, they finally stumbled to the corner store that was a block away from Dean’s place. 

“What are we doing here? I thought we were going back to your house,” Cas said, his voice low and slightly warbly. Dean pretended not to notice the tears, and pointed to the bakery display by the counter. 

Dean winked at Castiel, and waved his arms so Jo Harvelle, the sixteen year old daughter of the owner, would come and serve them. Jo ran her hands through her blonde hair, and looked ready to snap at the cocky twelve year old, when she noticed the flood of silent tears streaming down Cas’s face, and swallowed her venom. 

“What can I do for you boys?” She put on her best southern-comfort voice. 

“I’ll take a slice of apple pie, and anything the birthday boy here wants,” Dean slapped Cas on the back lightly. 

“I, um, can I have that?” Cas gestures to a piece of chocolate covered cheesecake in the center. 

“Now that’s what i’m talking about!” Dean said too loudly. Dean forked over a crumpled five dollar bill, with a wink and told Jo to keep the change in the coolest voice his head could come up with. Jo held back her overwhelming desire to smack the kid on account of his crying friend, and quietly put the pieces into plastic containers, which she slipped into one big brown bag, before passing it along. 

“Thank you,” Castiel mumbled quietly, his tears slowly subsiding. The pair walked out into the heat, and tried to continue to Dean’s. They turned the corner, and because the universe was feeling especially sadistic that morning, poor Castiel ran head first into none other than Gordon Walker and Meg Masters. 

Gordon remained on both of his feet, but Cas was knocked to the ground. 

“Oh look,” Gordon sneered, “It’s the most pathetic Novak and his idiot boyfriend.” 

Meg laughed, and then noticed Castiel’s tears. “Hey, I think the little angel’s  _ crying.”  _

Meg and Gordon’s laughter only increased as Cas struggled to stand, only for Gordon to push him down once more. 

“Not so tough without your brothers around, huh?”

“Enough!” Dean took a poorly coordinated swing at Gordon, due to the pastries in his left hand, and the larger boy caught Dean’s wrist. 

“How about you give us whatever’s in the bag, and we call it even, huh kid?” Gordon leered down at Dean. 

Out of the corner of his eye, Dean saw Cas get to his feet while Gordon held onto Dean, swing back, and kick the boy in the shins. In shock and pain Gordon released Dean’s wrist. Dean and Cas turned and sprinted in unison, around the back of the convenience store. 

Leaning out back, with a cigarette in one hand and a Three Musketeers in the other was none other than Gabriel Novak. The seventeen year old goofball had the decency to look sheepish for skipping out on his little brother’s party, but soon noticed the two boy’s frantic state. Before he could ask them what the hell just happened, Gordon, trailed by Meg, appeared in the opening to the alleyway. Gabriel may have been short for his age, but he was built like a truck, and could for-fucking-sure intimidate the hell out of any thirteen year old douche. He shoved his bar in his pocket, before gently nudging past Cas and Dean. He flailed his cigarette for added drama as he slowly asked, “Is there a problem here?” 

Gordon shook his head rapidly, and turned to see that Meg had already fled the scene. He followed her lead.

“Yeah you better fucking run!” Gabe turned on the two boys. “You kids alright?”

They both nodded shakily, and Gabe stubbed out his cigarette and pulled both the boys into a surprise hug. 

“We’re, uh, going to my house if you wanna, stop by or something,” Dean offered quietly. 

“Nah, I think i’m gonna do my own thing for a little bit. Oh, and Happy Birthday Cassie,” Gabe pulled out his wallet, and handed Cas a hundred dollar bill, “Sorry there’s no cake this year. I just can't go back right now.”

Cas nodded in understanding, before pulling his brother into one final hug. 

\---------

Dean watched with satisfaction as Cas slowly sunk comfortably into Dean’s couch, rewatching Star Wars for what must be the millionth time, munching quietly on his cake. 

“Oh, I almost forgot!” Dean reached into the deep pockets of his jacket, and pulled out the medium sized black book. 

Cas looked at him in mild curiosity, as Dean reddened as he handed Cas the book. 

“If you don’t like it, it was my mom’s idea,” Dean said, looking away, as Cas pulled the red bow off of the leather bound book. 

Cas opened up, and from the shiny laminated folds, five year old Dean and Cas stared back at him. A small genuine smile lit up his tear stained features, as Cas flipped gingerly through the past seven years of his friendship with Dean. He then put the book down very carefully on the coffee table, before he lunged at Dean, pulling the rigid boy into his arms.

“I love it,” Cas said, his face buried in Dean’s shoulder. 

“Well, then it was 100% my idea,” Dean grinned wildly, happy he succeeded in bringing Cas some joy on what has to be the shittiest of all shitty birthdays. 

“I’m glad, buddy,” Dean mumbled, the two boys holding on a little longer than strictly necessary. 


	4. Chapter 4

Lawrence, Kansas

_ 16 Years Ago _

  
  


“Lisa, I, I just can’t, I'm so sorry,” Dean buried his face in his hands, shame and guilt coursing hot through his body. Lisa crawled carefully over the itchy motel room bed, trying not to crease her midnight blue gown. Dean waited for her weight to leave the bed, to desert him and his fucking uninterested dick, but instead she began to rub small circles into his back. 

Dean felt himself starting to shake, and Lisa pulled him closer. 

“Shh, it’s ok. You are not broken,” Lisa’s voice took on an almost melodic rtone, as she spoke firmly in Dean’s ear, as if she was a mother consoling a grieving child. 

“There is nothing wrong with you,” she reiterated, and then louder, “Are you hearing me Winchester?” Dean finally looked up at her, his eyes shining. 

“I want to hear a ‘Yes, Lisa’ out of you,” Lisa gave him a small smile, invoking the memory of Mrs. Mills old catchphrase. 

“Yes, Lisa,” Dean said, almost believing himself. 

“Attaboy. Now it’s fine that you aren’t into me, or maybe even not into my anatomy in general. Maybe you’re not into anything at all! And if you’re into dudes, that’s cool dude too. Just don’t let yourself feel all this self hate anymore. It’s eating you alive.” 

Dean felt another wave of shame shake his body. He stared up at Lisa, sweet, funny, smart, and still smokin’ hot Lisa. She looked down at him, and he found himself unable to lie to her anymore. Maybe he wasn’t ready to scream it to the heavens, but he could whisper it to his girlfriend of one year. 

“Lis, I, think I’m gay,” Dean had never uttered his darkest fear out loud, and was slightly shocked when the world didn’t end. 

Lisa sighed, gave Dean a quick peck on the cheek, and said, “Now that the big gay revelation is over, how about we get your deposit back on this room, maybe some ice cream and we call it a night, huh?”

“You always know how to make me feel better Lis. I’m so so-” Lisa held up a finger, silencing the boy.

“I swear to God Winchester, if you try and apologize to me about your sexuality, I’ll rip you a new one.”

Dean sighed again, and stood, helping Lisa up off of the unused bed, “I wish things coulda worked out, is all,” Dean looked down. 

“Me too, Dean. And when I ask if we can still be friends? It’s not a request. It’s an order.” 

“Yes, Lisa,”

\----

Dean pulled up to his darkened home, the impala purring silently under his touch. He picked up the Ben and Jerry’s cup to his left, and attempted to sneak inside as quietly as possible. 

He entered the front door, closing the door quietly behind him. He froze, as he heard a familiar clinking. His Dad sat alone in the living room, too drunk to bother turning on the light for the dramatic effect John was obviously going for. 

“Oh look who’s back. I  _ knew _ you didn’t have it in you to screw her,” John laughed without humor, a harsh, grating sound. 

“Dad, I-,”

“Shut up, boy,” John held up a familiar red lettered magazine, and waved it like a death sentence, as he rose from his chair slowly. 

Dean started to back away, his mind aflame with a constant chorus of “I’m fucked, i’m fucked, i’m fucked. ” 

John got close enough to Dean that he could smell his rancid whiskey breath, as he breathed, 

“No son of mine,” John punctuated the last word with his fist, and Dean was too slow to cover his face. Dean was protecting the normal areas, not realizing that John was too drunk to care that he was hitting the boy in places people could see.

Dean let out an involuntary cry, and John pulled back to swing at him again, when his fist was caught. 

“No more,” Mary cried, gripping John’s hand tightly. 

John whirled around, and Dean felt even more terror flood his veins. If John laid a hand on Mary, Dean didn’t know if he could stop himself from killing the old man himself. John looked into his wife’s eyes, and deflated, dropping the magazine and stepping away from Dean. 

“Go,” Mary said to Dean, “I’ve got this.” 

Dean turned and raced from the house, his eye throbbing painfully, and slowly swelling. He hopped into the impala, his feet moving on autopilot. He found himself on the familiar hill, what he had always jokingly referred to as Mount Olympus. He realized belatedly that Castiel, and his terrifying mother, would probably both be sleeping, but it was impossible to un-ring the doorbell, so he waited nervously for Cas to answer. 

Cas opened the door slightly, his perpetual bed head even worse than usual, draped in a star wars t-shirt that was much too large for him. 

“Dean? Aren’t you supposed to be losing your virginity?” Cas asked in the tired monotone that Dean had learned was his sarcasm. 

“Can I come in buddy?” Dean swallowed nervously, shoving his hands into his wrinkled tux. 

“Of course,” Cas opened the door, and Dean stepped into the light. 

“Your eye!” Cas’s hands flew to Dean’s face, touching gingerly around the inflamed area. 

Dean tensed, but flinched away from Cas’s touch all the same. Cas drew back, and steered Dean out of the cold, minimalist living room and up the stairs. He sat Dean firmly on his bed, and held up one finger, before disappearing back down the stairs. Dean relaxed against the headboard, breathing in the familiar scent, the adrenaline finally starting to pour from his veins. Cas returned a moment later with a bag of frozen peas, which he pressed carefully around Dean’s eye. 

“What, no steak?” Dean began to laugh, but Cas didn’t crack a smile. 

“Raw meat can actually harm you in this instance, and has no healing properties. Dean,” He paused, and looked up at him carefully, “You have to be honest with me, who did this?” 

Dean looked at his fingers, and Cas let out a great sigh. “Fine, don’t tell me. I just hate to see you hurt.” The boy looked down, swallowing his next words, a faint blush creeping into his cheeks. 

“I’m so-,” Dean started, and Cas whipped his head up, fury alongside his tears. 

“Don’t you dare say you are sorry,” and Dean closed his mouth, and nodded. 

Cas’s expression softened. Dean stared up at his best friend, and there was so much he wanted to,  _ needed _ to tell him. Dean thought that, maybe he was ready, to lay it all on the line. The tension in the room, the tension in their  _ friendship _ for the past five years or so, had led up to this. Dean opened his mouth, and a cruel God took a glance his way, because at that moment his phone rang. Cas let go of the ice on Dean’s face, like he received a shock, and murmured an apology as Dean picked up the phone. 

“Hello?” His voice came out gruffer than normal. 

“Sweetheart,” His mother’s voice called to him, “The police came to get John. You can come home now honey. We have a lot to discuss.” 

“Ok, mom,” Dean said, suddenly a little boy again, as he hung up. 

“Cas,” and Dean watched his friend deflate. So he hadn’t made up the moment in his mind. He was tempted, so very tempted, to tell Cas what he really meant to his broken best friend. He had bared his soul once this evening already, what was once more, one that might actually bring him some joy. 

“Buddy,” Dean stopped himself. If Cas said no, if he didn’t want him, Dean was sure he would never be able to recover, “Buddy, I got to go.” 


	5. Chapter 5

“Daddy, are you in love with Mr. Novak?”

Emma looked up in surprise from her cheerios at the sound of her father spitting up his coffee. 

“I, um, well,” Dean stumbled, looking down at his daughter, his life, his love, waiting patiently for the answer to what she believed was a simple question. 

“Maybe it is that simple,” Dean thought to himself. He folded over his newspaper that was covered in Halloween ads already. Dean looked at his hands, and realized that if he were forced to pick a high point in his life, it would undoubtedly be the last month. 

Trips to the children’s science museum, the local one stage theater and a tiny bookstore when the outdoor film festival was suddenly rained-out played like a highlight reel through Dean’s mind. Emma had welcomed Cas into their family enthusiastically and immediately, and he fit perfectly. Every moment Dean spent with the man only served to draw him in further, not dissuade him. This realization was long overdue, from the moment Dean realized he was stupidly in love with his best friend on prom night, and was still too mired in self hate to be a man and tell him. After that night, the month leading up to graduation had been an absolute whirlwind. Final exams, combined with his father’s trial and subsequent jailing left Dean mostly shut in. Truth be told, the few times Castiel had tried to bring up that night, or anything of the kind, Dean shut down and brushed him off sarcastically. Soon, Cas learned not to bring it up anymore. 

John Winchester died one week into his seven year sentence of cardiac arrest. Despite himself, Dean cried the entire night. Dark thoughts infiltrated his mind. If he hadn’t been gay his father would have been home, and none of it would have ever happened. 

Mary had moved the boys away from Kansas shortly after that, all the way to California. He and Cas lost contact soon after the big move, and Dean knew that it was his fault too. Cas would call, and Dean would pretend to be too tired to talk,  _ timezones _ , he’d say, even though it made no sense, because those damn butterflies in his stomach took off every time Cas said his name, and Dean  _ should not have those feelings _ . 

By the time Dean had learned to love himself, when he realized that he could like both guys and girls, but preferred men, after many years of therapy and living in liberal California, it was far too late to rekindle whatever could have happened between him and the boy he used to call his best friend. Or so he thought. 

Maybe he had kept Cas, and himself, waiting long enough. 

“Yes, I think I am,” Dean said, finally answering his daughter. 

“Good, I like having him around,” Emma said, diving back into her cheerios.

“Me too, kid.” 

Dean arranged for Emma to be picked up by Lydia afterschool, called in sick to the office, and set to prepare the house. By the time three had rolled around, Dean had driven to three different florists, before picking the perfect bouquet. On a whim, he stopped by the bakery, and got a chocolate covered cheesecake, and an apple pie, hopefully to share with Cas, but also to binge eat if this whole thing didn’t work out. Dean prayed for the former, but he felt his self doubt creeping back as he gripped the steering wheel tighter. 

Dean leaned on Cas’s gray Honda, as the teacher exited school at about half past three. Dean studied Cas before he was noticed. Cas still wore a tie every day, just like his dickbag father had drilled into him, but it was pulled out, from him constantly fidgeting with it. He had his head down, and had a sleek leather jacket pulled around him. Dean wondered if he still wore trench coats, and decided to get him one for Christmas if he didn’t have one already. His hair was slightly ruffled, and Dean just needed to make it even messier, tug on the stray locks to make those baby blues that they frame stare back at him. Dean ran his tongue over his suddenly dry lips. 

Cas finally looked up, and a grin split his face as he almost skipped over to his car. 

“I was worried I wouldn’t see you today, ” Cas’s impossibly voice washed over Dean, and as much as Cas was still the boy he met in kindergarten, this was a change that Dean was very on board with. 

“I, uh, I have something to tell you, buddy,” Dean felt his voice failing him, so he cleared his throat, and locked eyes with his best friend. 

Cas waited patiently, though Dean could see him rocking slightly on his heels

“I love you. I think I maybe always have, and I was too stubborn to realize it. I’m so-” and suddenly Dean couldn’t talk anymore because Castiel’s tongue was doing  _ things _ to his mouth that he simply could not ignore. 

After several minutes, and a few catcalls from Cas’s co-workers, the two broke apart. Cas plucked the flowers from Dean’s grasp, and said “If you try to apologize to me one more time, I’m taking these and running.” 

“Ok,” Dean nodded, and pulled Cas in by his tie, sealing their lips together, and the rest of the world appeared to fade away. 

**Notes for the Chapter:**

> Follow me on tumblr ! @writerposer


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